With the High Holidays right around the corner, Rabbi Goldstein, usually in the days leading up to Labor Day weekend, will park himself at his desk, spread out all of the various materials — in the form of email messages, recorded iPhone notes, handwritten thoughts and bookmarked pages — that he’s accrued over the course of the year and embark on crafting his Rosh Hashanah sermon.

Rabbi Goldstein admits that he is not the most organized person, but realistically, even the highest level of orderliness could not account for the piles of potential notes, talking points and life events that have amassed from the time Yom Kippur ended in 2012.

And that is the task for Rabbi Goldstein, sifting through everything from the year that was, scouring it for the most significant forms of meaning to relay to his congregation. Oh, and he also has to do it in a timeframe that keeps his listeners interested and engaged.

Rabbi Goldstein said some of his colleagues have their Rosh Hashanah sermons written months in advance. Rabbi Goldstein’s sermon may be added to, edited or erased just hours before he ascends the bima.

“It’s a constant process leading up to hours before the holiday begins,” said Rabbi Goldstein, in his 18th year at Beth Israel. “Some of my colleagues have already written their sermons by May or June and have carefully, over the course of the year, begun that process; that’s never been my style. Every rabbi works differently in that way. … I’ve had the wisdom of knowing over 30 years of doing this that things change and require refocus.”

Rabbi Sander Goldberg of Nachal Chaim has cultivated his personal style, perfected over the course of four decades in the pulpit. He explained that at his Orthodox synagogue, the Rosh Hashanah sermons are of a different ilk than those of a Reform and Conservative service. And, he doesn’t take much time to prepare.

Rabbi Goldberg does go over reading materials and inserts paper clips into items he wants to directly quote or refer to. He then brings the content with him to the lectern.

He also explained that unlike some other rabbis, he very rarely, if ever, relates his sermons to a current event. Instead, he analyzes the Talmud and the Bible and goes into how it defines the meaning of Rosh Hashanah.

With more than 40 years of conducting High Holiday sermons, does Rabbi Goldberg ever worry about running out of ideas?

“There’s so much Torah to study, so many different aspects, so much Talmud and Midrash … that you’re not going to run out of things to talk about,” he said. There are hundreds and hundreds of books that talk about the holidays. Each and every one says something a little bit different. … That’s not to say that after many, many years I don’t repeat something I’ve said [before], but no one is going to remember it anyway.”

Rabbi Ron Shulman places a great deal of effort on relating his sermons to his congregation.(Justin Tsucalas)

Chizuk Amuno Congregation Rabbi Ron Shulman has his own take on the Rosh Hashanah sermon, and sermons in general for that matter. In addition to being a rabbi for 31 years, Rabbi Shulman was a professor of homiletics (the art of preaching) at American Jewish University in Los Angeles.

Rabbi Shulman speaks from a prepared text but also makes sure to communicate extemporaneously, meaning that he does not read directly from his notes and instead makes eye contact with his audience.

“You want to present your thoughts in way that will connect with the congregation,” Rabbi Shulman said. “I also think words matter, and you want to prepare carefully what you want to say, but let the mood of the moment impact the delivery.”

Rabbi Shulman also places a great deal of emphasis on relating his sermons to the congregation. Although he has been a rabbi for more than three decades, this is only his 10th year at Chizuk Amuno. He explained that it takes time to build a rapp-ort with a new congregation, and that the relationship is crucial to a meaningful sermon.

“Sermons exist in the context of a community and a congregation,” Rabbi Shulman said. “You have to know who’s sitting in front of you and you have to be thinking not only what interests you but what’s going to be relevant and important to them. I review the year, I look back at different experiences we’ve had together so that I have an understanding of who they are and what they are carrying with them into the synagogue.”